1951
Marilyn Monroe wears a pair of hot-pants with cowboy boots in a 1951 promotional shot for Valentine’s Day.
Marilyn Monroe wears a pair of hot-pants with cowboy boots in a 1951 promotional shot for Valentine’s Day.
Models on the runway during a May 1979 gala highlighting Ralph Lauren’s Western wear.
A still of Debra Winger wearing cowboy boots in the 1980 film “Urban Cowboy,” which also starred John Travolta.
Chris Westwood wears a Versace minidress with cowboy boots as she attends an Armani party at Studio 54 in January 1980.
Diana Ross wears a pink jumpsuit with white high-heeled cowboy boots in 1980.
Princess Diana teams sweatpants with cowboy boots as she takes son Prince Harry to school in the 1980s.
Cindy Crawford wears a gingham look with Western boots on the runway in 1990.
A model wears a strapless pink leather mini dress and matching cutout cowboy boots at the Givenchy spring ’98 show. Alexander McQueen designed the collection.
A model wears a white leather mini dress with a halter neckline and matching cutout cowboy boots at the Givenchy spring ’98 show. Alexander McQueen designed the collection.
Britney Spears wears Western boots at the Kids’ Choice Awards in 2003.
Sienna Miller wears a dress over jeans with cowboy boots at a 2004 film premiere.
A model on the catwalk at the Blugirl fashion show in September 2005.
A model wears slouchy Western boots on the runway in a fall ’09 show.
A model walks the runway in Western boots at the fall ’09 John Aquino show.
A model wears blue Western boots with a floral dress at Anna Sui’s fall ’09 show.
A model on the runway at Dolce & Gabbana spring ’10 in a white lacy dress with brown Western-style boots.
A model wears a red coat with Western boots in a look from the Michael Kors pre-fall ’11 collection.
A Western print dress with burgundy scrunch boots at the spring ’11 Anna Sui show in New York.
Sita Abellan wears a pair of funky cowboy boots with a musical print-look at the spring ’17 NYFW shows in September 2016.
Romee Strijd on the catwalk in a bathing suit and silver cowboy boots at the spring ’18 men’s/women’s resort Moschino show.
Hailey Baldwin wearing Off White x Jimmy Choo Sara white boots in 2018.
A model walking the runway in Western boots at the Schiaparelli couture spring ’19 show.